War Letters
by damonsass
Summary: What will you sacrifice for love? Your life? Will you walk into the valley of the shadow of death to bring your true love home? In the middle of the Civil War, Elena stops receiving letters from Damon. What risks will she take to make sure he is alive?
1. Prologue

**Elena's POV**

My dreams were tormenting me. I couldn't sleep. Sitting up in bed, I glanced at the clock. 6:43. So much for getting any extra sleep on a Saturday. Every time I closed my eyes, all I could see was him dying calling out in pain. My subconscious was torturing me. Getting dressed, I walked downstairs seeing our maid, Emily sort through the mail.

"Anything from-"

"No, miss.. nothing today," she replied. I sat down at the table as my mother and Emily began serving the family breakfast.

I hadn't heard from him in a month and a half. Yes, it did take a while for mail from the front lines to come through, however it had been too long. Letters usually took around two weeks to come through, but this was unacceptable. The third, fourth, fifth and sixth week I had written a letter each. No response.

Standing from the table, I walked out without even excusing myself. My mother, Isabelle snipped at me in anger about manners. Hardly paying any attention, I grabbed my wrap and my shoes before walking out the door to the barn.

The grass crunched under my feet from the frost. That was when I realized how early it was. No matter, I still trudged on. When I reached the stables, the stable boy was mending to my favorite Appaloosa horse, Versailles. Alongside my horse was my father's horse, Brandy, named after his favorite beverage. Seeing Brandy only pained me because it made me think of _him_. It was _his_ favorite horse as well.

Late nights, we would sneak out taking the horses for a midnight ride in the fields. He made me feel free. He opened my eyes.

"Aaron.." I muttered. He looked up doing double take.

"Miss Gilbert.. uh.. are you alright miss?" He asked seeing my bare feet and flushed cheeks from the cold.

"Aaron I need your help," I huffed.

"Sure, anything miss!" He nodded dropping the horse brush and standing with a slight stumble on a horse shoe.

"I need you to prepare the carriage. I am making a trip to the Salvatore manor immediately," I ordered. His face hardened slightly. I knew he had feelings for me, but I always acted like I didn't notice. He hated the Salvatore's.

"Miss.. I do not think your father-"

"Aaron, you already know he is not there. I am going to see Stefan," I sighed bending down to put my shoes on.

"You know he irritates me even more. He looks at you like you are a snack. I cannot allow it," Aaron shook his head looking down.

"Aaron, you work for me." I was beginning to become impatient. He giggled.

"I work for your father, Princess," he scoffed. My fingers shook as I tried the clasp on my shoe. I let out a breath in anger. "Here," he knelt down at the same time I stood clasping my shoe before beginning on the other one.

"I am serious. I just need to talk with Stefan. You can come if you please," I offered. I was rather good at bargaining.

"So be it," he sighed standing and rubbing his hands together. "I will get Versailles and Brandy ready."

Once the carriage was ready, we were off.

"What is making you want to talk to Stefan Salvatore?" Arron asked as he parked the carriage in front of the Salvatore manor holding out his hand to me so I could step down without falling. "You have never wanted to say a single word to him before. What is different now?"

"I think his elder brother, Damon, is in trouble. He hasn't responded to a single letter of mine for over a month," I teared up just saying it out loud.

"Maybe he just moved stations. It happens all the time in the military. My father is a veteran from the Black Hawk War back in '32 and he moved stations a lot, so it was hard to contact us. There is no need to worry, miss," he assured me. Aaron was being polite, and that never usually happened when the Salvatore's were involved. I shook my head.

"I know when something is wrong with him. I know. I love him.." I choked out beginning to cry.

"Miss Gilbert, I assure you we will find out what happened to him," he nodded his head.

I paused gathering myself and wiping my eyes before taking a step up to their door.

"Aaron please wait by the carriage," I asked as politely as I could. He hesitated until I gave him a stern look. Backing off, he went and stood by the carriage.

Damon's mother opened the door and smiled warmly. She always had a soft spot for me. His father on the other hand did not. Stefan over time developed quite a cold spot in his heart for me as well.

"Elena, dear, come in it is freezing. Helen is making breakfast for us. You should join," she offered.

"I apologize Mrs Salvatore.. I cannot stay for breakfast. I merely came to talk to Stefan about Damon. Have you heard from him in the past month?" I asked inwardly crossing my fingers hoping he was at least replying to them.

"No.. we haven't heard from him since he left about six months ago. You've been hearing from him?" A relief came across her face.

"Damon has been writing every two weeks to me, however, I have not received anything in a month and a half. I'm greatly worried.." I began to cry again just as Stefan's face appeared in the door. His expression cold as his jaw clenched.

"What are you here for?" He asked.

"Manners, Stefan!" His mother snipped. Stefan disregarded her comment.

"May I please talk to you?" I asked. Stefan hesitated before nodding walking out the door. Offering his arm, I took it walking with him. Aaron stood straight and alert watching us walk by. I nodded showing him I was alright before focusing my attention to Stefan.

"What would you like to talk about?" Stefan asked as we walked leisurely on the pavement. He seemed to relax. I knew he still cared for me, but he tried his best to follow his father's example and not care for anyone. I knew he would eventually break. Stefan's heart was nothing like his father's. Damon was the complete opposite of his father.

"Damon.. I was wondering if he was writing to-"

"Elena!" He dropped his arm completely letting my hand fall to my side.

"Don't even start, Stefan! I know you're worried about him as well! I know I broke your heart, but you know _just_ as well as I do that you and I were _not_ meant to be together. I also know that Damon has been writing to you. Your father may be hiding it from both of you, but I know he's been writing, and you do too. I'm going _crazy_ thinking if he's been kidnapped or if he's dead, and I can't even think-" I broke down not understanding my own words bursting out of my mouth.

Stefan was rubbing my back softly and gently hugged me.

"Follow me," Stefan held out his arm. I clung to it for dear life trying to quiet myself.

Leading me to his house, we walked in and upstairs to his bed chambers.

"Stefan.. this is not appropriate at-"

"Shh!" He hissed patting the edge of his bed. I did as I was told, which was a first, and sat down where he told me to. Going through his dresser, he pulled out a wooden box and gently closed his door. Sitting down next to me, he laid the box on my lap. "Father says if I tell mother, he will burn them all. He says if she doesn't hear from Damon at all it will help her deal with the loss better if Damon doesn't return home. He would more than likely skin me like the cattle if he knew I was telling you, so if you mention this to him just know that you are signing my death certificate," he raised his eyebrows.

"That's barbaric that you aren't allowed to tell your mother. He is her son as well, not just Giuseppe's," I argued.

"Elena.. promise me," he raised his voice slightly.

"Yes, I promise," I agreed rolling my eyes. Stefan nodded opening the little box to about a dozen letters. I teared up just reading his handwriting. They were addressed to "Lillian and Stefan Salvatore" each and every time. His grudge against his father for signing him up for war was impressive. I didn't blame him, though.

"You should read this one.. I think you'll find it helpful as to why he may not be answering your letters," he picked the top one off the pile handing it to me. It was the most current dated one. The top one was only addressed to Stefan. I nearly ripped the paper open trying to read it.

 _Stefan,_

 _I fear the southern troops are not as strong as they once were. The Union Soldiers have been taking more and more of us every day as hostages. Some they take, we find days later in ditches. They are usually the weaker ones. They may be killing off the weaker men and keeping the stronger as hostages._

 _What has this country become?_

 _Please, I only addressed this to you because I do not want mother to worry. I apologize for pouring my heart out about the true natures of war. I cannot tell Elena anything of the sorts. I usually just mention how we sit around smoking and playing poker. I cannot tell her the truth, but the civil war is the worst thing I've ever experienced. I am worried to never see you or her again._

 _I truly despise father for this. Please, if I stop writing letters, I am more than likely dead or have been taken. I want you to help Elena move on. She deserves the world and so do you. Move on Stefan. Be everything father is not. He is not a true man. You are. Find a nice woman and settle down... but keep your paws off my girl.._

 _I love you, brother._

 _Damon_

I closed my eyes. Standing, I set the paper down on Stefan's lap. Without a single word, I walked out of his room, the house and began to run. I ran past the carriage with Aaron nearly screaming my name. Not a single tear escaped my eyes as I ran. My shoes in one hand, and the edge of my dress in the other so I wouldn't step on it.

I ran for nearly twenty minutes before coming back to my own house. Aaron was right on my tail yelling at me to get in the carriage. Ignoring him completely, I threw my shoes to the ground opening the front door of the house. My mother came to the door along with my father and brother when they heard the commotion, and all began to yell asking where I was. All I heard was white noise.

Walking clear up to my bedroom, I pulled out a blank sheet of paper and began to write before I stuck it in an envelope addressing it to his station. Opening a suitcase, I packed only essentials before walking back down stairs in my riding attire. I walked past my family who was still asking questions, out the door, and shoved my letter into the mailbox before getting on my horse and riding off into town.

 _Damon,_

 _I am coming for you._

 ***yay I hope y'all like it so far! I'm going to try to write in the past and use as many historical facts as I can because I always wanted to write a Delena story in the 1800's and this is the route I'm taking! Let me know what you think of the prologue! You will get more info in chapter one so no worries there but just wondering how it looks so far?:) let me know with a review or two! If there are errors or you don't understand me let me know because I wrote and reviewed most of this at 2AM! Thanks! -Syd**

 **2053 words**


	2. Chapter 1

**Elena's POV**

"Elena you look a mess! Did you even sleep last night?" My mother shook her head as I sat down at the breakfast table. "You have bags under your eyes. Trudy will have to fix you up before we leave today," she sighed turning to her breakfast.

I breathed heavily trying to tell myself it was just Mother being Mother, but my patience was thinner than a needle this morning. I turned to my omelette Emily had sat down in front of me taking a bite.

"Emily, I will never underestimate your cooking skills ever again," I moaned taking another bite. I was trying immensely to make today positive. Guaranteed I knew it would be one of the worst.

"I will hold you to it, Elena," she laughed taking my cup and filling it up.

"Manners, Elena, and sit up straight. You must learn to dine as a lady... not an animal," my mother snipped across the room raising her teacup to her mouth properly. I did as I was told and sat up straight before looking back to Emily. She winked at me.

We had nearly grown up together, Emily and I. She was my best friend along with my brother Jeremy.

Emily's birth mother had dropped her off on our doorstep for work at the age of seven when in all reality her she had abandoned her. My parents had taken Emily in as one of their own adopting her.

My family was unlike the rest of the south. We welcomed everybody, no matter the color of skin and treated everyone as equals. Though Emily's dark complexion stood out among the rest of my family, no one had ever seemed to question it. Especially since my father was one of the most wealthy of men in the south.

He owned over three fourths of the clothing companies in the south. My mother, Isabelle, was wealthy as well. Her profits belonged to my father making him even wealthier. Mother's father used to be in a mining business and struck gold further south. She was new money, but she acted like her family had been in the game for generations.

"What's for breakfast?" Jeremy asked panting as he jogged down the stairs.

"Emily's omelettes of course!" My father chuckled coming down the stairs kissing my cheek, Emily's cheek and my mother's cheek before sitting down.

"I thought it was Elena's turn to cook?" Jeremy asked sitting down.

"Do you really wish for this brand new house to burn down?" Emily asked raising an eyebrow.

"Hey!" I laughed collecting my mother's and my own dishes before ushering Emily to sit down and eat.

"I'm only saying we just moved here. It would cost father a lot of paperwork before having to build a new house," she shrugged with a laugh.

"Right you are, Emily," my father nodded shoveling his omelet in his mouth. My mother looked up at me before pointing at my father.

"If you want an example of what you look like while eating, just look at your father," she raised an eyebrow at John causing him to sit up straight and slow down.

My mother was rather stern, but that didn't stop us from having our fun.

"Oh relax Mother, it is only Emily's cooking that gets me that way," I winked at her. Isabelle shook her head and stood excusing herself. Looking to Jeremy, I realized he was still panting as he scarfed down his food. "Why are you so out of breath and sweaty?" I asked picking his plate up.

"Does nobody have table manners in this household?" Mother nearly yelled. Jeremy ignored her.

"I have been getting into shape. I went for a run this morning and was just doing some stomach workouts in my room." He smiled.

"Jeremy," my mother said in a warning voice. "You are only fifteen, son. There is no need to worry about such issues yet," she smiled slightly.

"Nonsense!" My father interjected. "He is a man now, and he needs to start looking like one," he winked at Jeremy. "Son, why don't you go wash up. You will come with me today to work today to learn the business. It is time," John smiled.

Jeremy looked down and nodded. There was no use in arguing with him again. He never wanted to take over for father. Jeremy's passion since he was little was to be a police man or in the military. Mother and father would not have it, however, he was the only man in the family the legacy of John Gilbert would pass on to.

"Elena, you go wash up as well," my mother commented. "Then we can go meet the Salvatore's for lunch." I nodded with a stand, however, my insides were screaming.

Speaking of why I did not sleep last night... I am to meet my fiancé today. That's part of the reason why we moved back to Mystic Falls along with my father's booming business. On top of that, my father had founded this town before I was born. Along with the Gilberts, the Lockwood family and the Salvatore family had also founded the town of Mystic Falls.

I walked upstairs to get dressed along with Emily. Trudy was just behind us.

"I know... I know how you feel," Emily looked at me from the side as we reached the top of the stairs. "I am to meet my future husband tomorrow as well. Father told me the youngest Lockwood boy would take my hand. His name is Tyler," she paused hesitating.

"What is it, Em?" I asked.

"I know color matters to none of you. We are family, but I have feared this moment for a long time. I know father would not choose a family that wouldn't be as accepting about my color, but I am still worried. What if this Tyler is putting on an act and treats me as a lesser person than I am when we are married?" She asked sitting down on the edge of my bed.

I sat down on my chair facing Trudy as she prepared to touch up my makeup and hair for the date.

"We will tell father if that happens, and he will find you a suitable man. You know father would do anything for you. He loves us all, and no matter the money, he would make sure we are treated respectfully," I nodded at her as Trudy finished up my makeup and moved on to my hair.

"You are right, I don't know why I am so nervous," she chuckled nervously.

"I am nervous as well, Emily. We are meeting our future husbands soon. It is probably from the move from Louisiana back to Mystic Falls. It was a long journey yesterday, and we need rest," I concluded trying to find a reason for my nerves.

"What is the name of the man you are to marry?" Emily asked trying to flip the subject onto myself.

"His name is Stefan. Stefan Salvatore," I looked down. "I heard he is handsome. I was engaged to his elder brothers first, but I am not sure who he is. Father decided to wed me to Stefan instead. He has not been mentioned a lot whenever father talks about the Salvatore's," I shrugged.

I couldn't wrap my head around the fact that I was going to meet my fiancé in just a short while. I didn't want this right now. I wasn't ready, and here father was pressuring me to marry a man I have never met. My stomach churned thinking about how I would soon be wed and not living with my family anymore.

"I don't know if I can do this."

"You are ready, Miss Gilbert," Trudy smiled gesturing to the mirror.

"Thank you Trudy.. and please call me Elena," I said quietly before standing. A knock came to my door. "Come in.." I sighed attempting to contain myself from crying. Jeremy poked his head in to make sure everyone was decent before coming in with a very becoming suit on him.

"Elena will you help me with this tie? I've never done one before and I've seen you fix one on father," he handed it to her frustrated.

"Yes of course, Jer," I smiled quickly taking the tie and swinging it over his neck before working on it.

"Lena what's wrong?" He asked taking my hand. I always had a soft spot for Jeremy. He and Emily were always there for me.

I lost it.

"I don't want this, Jeremy.." I cried trying not to ruin my makeup. "I don't want an arranged marriage!"

"I know, Elena.." he encircled me in his arms as Emily stood beginning to rub my back. "I heard Stefan Salvatore is a good man.. well, he is my age actually so almost a man," he smiled down at me.

"I don't even _know_ him," I laid my head on his chest. Jeremy was growing up. Sometimes it was hard to watch as I always saw him as my little brother who always pulled my hair when he didn't get what he wanted. Now he was going with father to work for business and began filling out. He was becoming a man.

"You'll get to know him.. and if he is not what you desire, I will do everything in my power to get father to reconsider," he said pulling away just far enough to wipe my eyes. "Okay?" He asked taking my chin so I would look up at him. I nodded hugging him once more.

"And if he hurts you or touches you inappropriately, I will kick his ass," Emily chimed in which caused me to laugh, turn and hug her.

"I on the other hand would kill him," Jeremy chuckled before his face went back to serious. "What do you want Elena?" He asked. "What are you looking for in a man?" I paused for a second before responding.

"I want a love that consumes me. I want passion, adventure and even a little danger," I responded. Jeremy smiled squeezing my hand.

"If this man does not give you that, then I will help you find the one that does," Jeremy kissed my hand quickly, and I almost began crying again.

"I love you both. I don't know what I would do without you," I smiled. "Oh and I would also like to be respected, so put that on the list," I added causing them both to chuckle. Jeremy nodded.

"Well, lets get Trudy to fix up your makeup again," Emily smiled calling out to her in the hall as I nodded and finished tying Jeremy's tie.

"We will make your wedding the most beautiful wedding of the century," Emily smiled at me.

"I don't feel like it's my wedding... I feel like I'm being sold," I looked down.

"That's the price of being a wealthy business man's child. _None_ of us end up with the things we want in life," Jeremy looked down. "For you two, I will make sure the opposite happens," he smiled before walking out.

His comment sent chills up my spine. Father was a very loving and caring man, but when it came down to big decisions regarding our lives, we had no say at all.

"Are you ready?" Emily asked me placing her hand on mine. I nodded. I would have to get this over with. Maybe Stefan Salvatore wouldn't be so bad after all.. hell maybe I would fall for him anyhow. Maybe he would be everything I wanted. There was only one way to find out.

"Let's get going, Elena. The entire Salvatore family is waiting for us, well besides Giuseppe. He will be working," she said as I made my way down the stairs. "I told him it will just be you and I. Everyone else is busy with work," she smiled.

"Emily's not working.." I furrowed my brow confused.

She cleared her throat looking from the ground, to me and to Emily.

"The Salvatore's aren't people who favor.."

"Go on you can say it, Mother. It doesn't offend me," Emily claimed politely.

"The Salvatore's do not favor colored people.." my mother choked out. I could tell she was going to have a hard time with this family, and so would I.

"No!" I nearly screamed angrily. "I will not marry someone who does not accept not only my family, but what I believe. Mother how could you?!" I shook my head.

"You _know_ it's not my decision, Elena. It's your father's," she looked down too ashamed to look up trying to stay calm.

"Bull shit!" I yelled. "He listens to you!"

"Language! Elena!" My mother was dumbfounded that word had come out of my mouth. I never usually cursed. It was not lady like to curse, but no matter, sometimes a girl must let off some steam.

"I refuse to go!" I yelled.

"Elena.." Emily grabbed my hand. "Go. You must," she insisted. "It's okay," she nodded. "Go see if you like this man, and if you have doubts then you know father will find another man for you. Maybe he's the one, you have to go," I knew he wasn't, but here I was nodding my head.

Embracing my sister, I squeezed tightly as my mother tugged on my arm.

"We are late, Elena. We must go," she turned to Trudy. "Tell Aaron to get the carriage ready," she ordered. Trudy nodded obediently rushing out of the room. I followed my mother down the stairs mentally preparing myself for what was about to happen.

I wasn't ready for a husband. I wasn't ready for that step. I was only eighteen years old. Even if I _was_ mentally ready for that step, I was overwhelmed with the move. We had just moved from west back to Mystic Falls, Virginia where my father grew up and I was born. He had always planned on returning, and this engagement had been in place for about a week. Before that, I had been engaged with his elder brother since I was a child. Giuseppe Salvatore had made the switch last week, and I was thankful.

Stefan and I knew each other a little better. We were the best of friends until the age of four, and then we moved west for my father's business.

I didn't even know what he looked like. I remember his raven haired elder brother on the Salvatore property tending to whatever work his father put him to. The raven haired boy always got into trouble, but I didn't know why. Stefan explained that his brother was five years older and had responsibilities that he would one day have. I had never met the raven haired boy, but I'm sure I would now at this lunch.

However, he was not the one I was worried about.

As Aaron brought the carriage around, he helped my mother and I in and we rode off to the Salvatore manor.

I spent the entire ride looking straight forward avoiding whatever my mother told me. She had spent the entire ride telling me how to behave and be a proper woman. Every once in a while, I would answer simply: "yes, Mother," or "I will, Mother."

Once we reached the estate, I looked out the small window and realized why my mother and father wanted me to wed this man. The Salvatore mansion was nearly twice as big as our own. The gigantic brick building stood boldly with its back against the trees. The road curved into a circle, and in the middle was the most gorgeous fountain I had ever seen. They had certainly upgraded their property since I was a child.

My heart sank. Father was only invested in the money of the transaction. That's why he was so eager to wed me so fast.

The door opened to the front of the house and two men and a woman stood outside on the porch awaiting my mother and I. Aaron parked the carriage and opened the small door holding his hand out to me. I thanked him as one man stepped down from the porch walking toward us. The woman stayed on the porch with the other man and raised her chin to show her superiority.

Once the sandy haired man came closer, he smiled at me.

"Elena?" He asked.

"Stefan?" My smile grew a small bit. He nodded. "Well you've definitely grown," I chuckled nervously causing him to laugh.

"Yes I suppose," he smiled shyly. I looked to the porch where the woman and other man seemed to be having an argument. This man I knew was Stefan's brother. I could never forget his curly raven colored hair. He shook his head and walked down to where we were.

Stefan walked over to the raven haired man and made him pause to talk to him. I walked to Aaron.

"Who is that?" I asked nodding to the raven haired man. The thing was, I knew exactly who this man was. He was Stefan's older, cunning brother. I never got around to his name, however. These brothers were the most attractive I had ever met, but the elder brother surpassed Stefan tremendously in that area.

"That is Damon Salvatore, Miss. He is Stefan's elder brother, however, I would steer clear of that one. From what I hear, he is big trouble," Aaron whispered back as the two men turned to us and began walking back. Damon looked upset at whatever Stefan had told him.

His icy blue eyes met mine, and he smirked. Chills ran up my spine and the back of my neck.

"Mrs Gilbert?" He asked looking to my mother and offering his arm. Stefan looked up to his brother before down at me.

"Elena?" He offered his arm mimicking his brother, and I took it shyly. I could feel his elder brother glancing over at me on the other side of my mother, which caused me to heat in embarrassment and uneasiness.

Their mother, Lillian, greeted us on the porch and invited us inside.

"Please, have a seat. I will tell the cooks to hurry along," she gestured to the parlor. We nodded taking a seat on the couch. "Boys! Make them feel welcome. They journeyed very far yesterday," Lillian snapped. The men nodded at their mother before both of their eyes met mine. I looked back and forth between the two.

"Would you ladies like anything to drink?" Damon asked politely pouring himself a glass of bourbon. My mother shook her head as I nodded. "What would you like Miss Gilbert?" He asked as his beautiful ocean blue eyes met mine.

"I will take a glass of bourbon please," I nodded to his hand before feeling my mother's tighten on my arm. The men stared at me in awe. It was unnatural for a woman to drink brandy or whiskey, especially a woman of my age. Women usually drank champagne or wine, but I enjoyed the acquired taste of whiskey.

"She will have a water," My mother corrected before giving me her classical 'you-messed-up-Elena' look.

The dark haired man hesitated before giving a subtle nod pouring me a glass of water.

"My mother mentioned you just moved here yesterday. Do you enjoy coming back?" Stefan asked glancing from my mother to me.

"It has been transitioning smoothly. I miss this quiet town," My mother smiled genuinely.

"The only thing I remember about this town is your front lawn. We played all the time, and I remember you getting in trouble all the time," I giggled at the raven haired man. He smiled genuinely as I stood to get my water. I walked over to him as he handed it to me.

"I remember that as well," he smiled. "And please call me Damon," he reached for my hand pressing his lips to the back. His eyes never left mine, and I could feel my cheeks heat. Stefan let out a little cough in the background to gain attention.

"Dinner should be ready shortly, why don't you ladies head to the dining room. My brother and I will gather the drinks," he claimed with a straight face.

I knew Damon would be yelled at by Stefan as soon as we left the room, but I did as I was told anyhow. I didn't do drama.

My mother leaned in close to me as we walked out of the room.

"Stay away from Damon, do you hear me?" She ordered. I nodded subtly entering the dining room. Hearing the men bicker in the other room was rather entertaining to listen to in the quiet room. I could hear Stefan yelling at Damon about staying away from me. Damon was arguing back saying he was only being polite.

As they entered the dining room, so did the meal. A beautiful salmon lunch was prepared for us. Stefan took a seat next to me as Damon and Lillian took a seat on the other side of the table.

The lunch was quiet until my mother broke the silence.

"So, Stefan, what kind of business is your father into?" She asked even though she already knew the answer.

"My father is managing a tobacco company, and he is working on a new product up in North Carolina with one of his coworkers. They're calling it a cigarette. It should be ready soon, but I'm not quite sure what it is," Stefan chuckled looking me up and down before returning to his meal. Damon cleared his throat.

"My brother will be taking over the mining business. I however, will be jumping out on a ledge. I will be taking over the cigarette company as soon as it's up and running," Damon smiled.

"Is not that a little risky, Mr Salvatore?" My mother asked with a raise of her eyebrows.

"Mother!" I whispered.

"No, it is alright. And please call me Damon. Mr Salvatore reminds me of my father, and I would rather be referred to as a sewer rat than my father," he chuckled.

"Damon!" Lillian scolded. The man rolled his eyes.

"As to your question, Mrs Gilbert, I am quite sure with this transaction. What is life without a little risk? I want adventure, so here I am," Damon smiled glancing at me before Stefan interjected.

"I would be careful brother! I already have a fiancé, which means soon I will be stepping up in the company. I'll believe your business transaction when you find yourself a wife," Stefan chuckled laying his hand on my wrist on the table. My face heated on embarrassment, and I excused myself.

I nearly ran to the restroom in tears. I didn't know what to think anymore. Stefan was extremely too forward for my liking or comfortability. I leaned over the sink trying to control my breathing. A knock came to the door.

"Elena?"

It was Damon.

"Just a second!" I called out running my fingers under my eyes to catch the smeared makeup. I opened the door. "Yes?" I asked.

"Are you alright, Miss?" He asked. I nodded my head holding it high. Damon rolled his eyes. "Follow me," he began walking. I hesitated before following him at a safe distance.

Everyone kept warning me about this man, but I hadn't seen anything too explicit yet. He took me to the parlor gesturing for me to sit down. I sat as he walked over to the don opening it and pulling out whiskey. Pouring a glass, he handed it to me.

"Drink," he ordered. "But, don't tell your mother. She might kill me," he chuckled.

I threw my head back downing the bourbon.

"Wow, you can take your alcohol well," he raised his eyebrows.

"Please, Damon. I need silence," I breathed resting my head in my hands. After a little while, his fingertip lightly brushed against the back of my hand.

"We should get back, they are probably missing us... well... you," he smiled looking down at me extending a hand. I let out a small laugh taking his hand as he helped me to stand.

"Sorry folks, Elena was just helping me pick out another wine," he smiled as we entered the room. Stefan's face went cold.

After we sat back down, the lunch nearly lasted ten minutes longer before Lillian and my mother decided it would be best to leave. The men had kept making snide comments throughout the meal at one another, and it was making me rather uncomfortable. Stefan had barely said a couple words to me at the table.

As we stood and excused ourselves, we said our goodbyes and promised to have lunch again.

Lillian hugged us both whereas Stefan shook our hands. Damon eyed me from a distance with a slight squint as if he was trying to figure me out.

As we walked out the door and to the carriage, my mother had gotten in and was waiting for me.

"Miss Gilbert!" Stefan yelled behind me. I stopped before the carriage looking back at him.

"Yes Mr Salvatore?" I sighed.

"Would you mind if we took a walk?" He asked. I looked to Aaron.

"Mr Salvatore will take me home," I nodded. Aaron was hesitant, but nodded. I turned and began walking with him around the property.

"I wanted to apologize for my crude behavior during lunch," he said solemnly coming to stand next to me at the carriage. "I didn't mean to make you uncomfortable."

"Yes you did, Mr Salvatore," I held my head high. He may be handsome, but that gives him no excuse to treat a lady like that. "You treated me as property to make your brother jealous... I will be treated as a person, nothing less. An equal."

"I just recently found out about your near engagement to my brother. My father promised to wed me first. Once a Salvatore is wed, they can be fully invested in the mining company. When you came back from town, my father planned on wedding you to Damon, but your father disagreed," he looked down.

Holding out his arm, he smiled at me. I held my head and kept walking. Putting his arm down, he sighed.

"I didn't really mind. I was just excited to be a part of my father's company..." he stopped causing Elena to stop looking up at him. "But then.."

"But then what?" I raised my eyebrows.

"But then I saw you," he took a step closer.

"There is more to me than my looks Mr Salvatore," I nearly rolled my eyes.

"Yes, I know. I saw something in you. It was like a spark of energy. You're no average lady Miss Gilbert," he smiled taking another step forward. "Your defiance is extremely attractive, and Damon noticed which caused me to get angry. Damon would not be able to handle you," he smirked taking a step forward as I took a step back.

"Excuse me? I will not be handled like some-"

He leapt forward shoving his lips on mine. The aggression overwhelmed me as he pressed his body to mine groping my hips. The kiss lasted nearly two seconds before I shoved him off and struck him across the face.

"Who in the hell do you think you are?" I breathed getting angry. He raised his eyebrows rubbing his face. "You immature little-"

"Is there a problem out here?" A familiar voice asked. I looked over to Damon on the porch. His arms were crossed glaring at his younger brother.

"I will just be heading home," I turned to glare at Stefan.

"I will take you back," Stefan offered.

"No!" I yelled.

"Elena, your carriage is gone. You need me to take you back," he grabbed my arm. I got out of his grasp.

"I would rather walk home," I held my head high. I was no rag doll to be tossed around. There was no way in hell I would marry this immature ass.

"I will take you home, Miss Gilbert," Damon chimed in stepping down from the porch to meet us halfway.

"Back off Damon," Stefan whispered standing a little taller.

"You wouldn't want your future wife to freeze her toes off now would you Stefan? She's _clearly_ not going to be riding with you, so I will take her." Damon held out his arm to me. I took it stepping away from Stefan. He may be dangerous, but I would have done just about anything to get away from Stefan at that point.

Stefan opened his mouth to protest. Before he could get a word in, Damon interrupted him.

"Don't worry brother, I would never touch a lady without her permission," he sneered. I almost smiled at his comment as he walked me toward the stables to prepare the horses.

"Thank you for that.." I mumbled looking down.

"My brother is young. He knows not the proper way to treat a woman. Stefan will learn, I will make sure of that," he nodded letting my arm fall to gather a couple horses.

"You know not the proper way to look at a woman. You Salvatore men look at women like they are your favorite meal," I raised an eyebrow.

"Making my brother jealous with our exchanges of glances was a plus, but you took my breath away. I apologize making you uncomfortable. It was not my intention. You're a very unique woman... in a good way. You've got fire. It caught my attention. My brother is a lucky man," he smiled at me before looking down.

"Where is your stable boy?" I asked changing the subject. I was also wondering why Damon was the one preparing the horses.

"We don't have one. Father caught me snooping in his work study a couple years ago. He fired the stable boy and made me do his job as punishment. However, I don't get paid," he shrugged gathering two black horses out of their stalls and attached them to the carriage.

"I sensed you were still a trouble maker," I giggled before pausing. "Wait.. he's _still_ making you do it?" I asked scrunching my forehead. Giuseppe Salvatore sounded like an awful man.

"No, Miss Gilbert. I do it for fun now. Tending to the horses is how I get away from that house and all of my duties to the family legacy. Father thinks it's madness, but I enjoy it," he smiled. Those baby blue eyes of his melted into my core.

"You work to relieve stress?" I asked with a small chuckle.

"It's hardly work, Elena. I will show you sometime, but you must wear your riding outfit. Don't want you getting those beautiful dresses dirty," he nodded to my outfit before lingering on my breasts and then back up to my eyes.

I still didn't know what to think of this man. He was a gentleman one minute, and then the next he was making inappropriate innuendos and staring.

Holding out his hand to me, he opened the carriage door.

"If I am to get the experience, then I suppose I should sit up there with you," I pointed with a smile. He nodded.

"Of course, but I will need to lift you up, is that alright?" He asked. I hesitated slightly before giving him a subtle nod. "Okay, put your hands around my neck to balance yourself," he ordered. I did as I was told blushing slightly as his body came closer to mine.

His body lowered as his knees bent scooping me up under my rear. Damon's face was parallel with my breasts, however, he looked the other way to make me feel more comfortable.

Placing me up on the seat, he climbed up himself squeezing in next to me.

"This is silly that we're directing a carriage with no riders," I giggled which caused him to laugh.

"You know how to laugh," he smiled. "I suppose it is strange, but it's an adventure," he shrugged. "I peg you as a woman who enjoys a little adventure in her life," he looked me up and down with a smirk which caused me to blush. He sure knew how to talk to women, but I already knew these Salvatore men were anything but gentlemen. Damon was the closest thing, however, he purposefully looked me up and down every once in a while before making sly innuendos.

His brother was intolerable and was not smooth about being a "bad boy". However, I don't know what it was about Damon, but he gave me an inward feeling. Every time he looked at me, my stomach would heat along with my cheeks.

"Elena?" Damon asked. I snapped out of my trance.

"I apologize, Damon. Yes?" I asked looking up to him. He handed me the reigns.

"Would you do the honors?" He asked with a smile.

"Of course," I smiled giving them a small whip towards the horses's behinds telling them to begin walking.

"I never realized how beautiful the trees are this time of year. This view is much better than inside the carriage," I smiled looking around the wooded area around the road. I could feel Damon staring at me as I watched the scenery.

"The most beautiful thing I've ever seen," he answered not moving his face.

I didn't dare look at him. I barely knew this man, anyhow.

We mostly sat in silence enjoying the chirps of the birds and sounds of nature on the way to my family's property. Once in a while we would make small talk.

As we reached my property, Damon taught me how to halt the horses. When we parked, he jumped down from the seat and helped me down.

"Thank you for the ride, Damon. I really appreciate it," I smiled at him genuinely before walking toward the house.

"Elena?" He asked. I turned around.

"Yes?"

"I got you something," he held up a bottle of bourbon handing it to me. "Do not tell your mother.. or my brother," he chuckled.

"Thank you, Damon," I laughed taking the bottle from him and turning around.

"When will we see you again?" He asked.

"Tell your brother to keep his paws off me, and then we can talk Mr Salvatore," I raised my eyebrows. "I have a question..." I paused.

"Anything."

"Everybody is telling me to stay away from you. What is that about may I ask?" I raised an eyebrow. He almost looked hurt by my statement.

"That is... um... a story for another time, Elena," he smiled. I crinkled my forehead confused, but nodded anyhow. "Very well, I will come pick you up tomorrow afternoon for riding," he smiled. "Goodnight, Elena," he winked at me. I shook my head blushing and walked in the house.

As soon as I closed the door, their was a sharp pain against my cheek. My mother had just slapped me.

"You will not be seeing Damon again do you understand, Elena?" My mother asked.

"He was kind to give me a ride home, Mother. Nothing happened," I tried to calm myself.

"You are engaged to his brother after all."

"Yet I was supposed to marry Damon, but father refused. Why is that?" I asked curiously.

"Do you not know about what happened to his sister?" My mother looked concerned.

"I just met this family today, Mother. They have a sister?" Isabelle's face fell slightly. Her anger disappeared into sorrow.

"Their sister died seven years ago... at Damon's hands."

 ***Wooooo first chapter is done! Let me know what you think! I wrote most of this around 3AM so no judgement. If something doesn't make sense let me know and I'll help explain! Please review and let me know if you enjoyed it! Thank you. -Syd***

 **5974 Words**


	3. Chapter 2

**Hey y'all I'm sorry it's been too long. I want to warn you Giuseppe will be in this chapter and he is an** _ **extremely**_ **racist man. You will be hearing him refer to people of color with the "n" word. I HATE this word, however back in this era and down south, this word would have been used a lot. I will use this word as least as I can, but just a forewarning that this word/racism/sexism will be in this chapter and most likely any that Giuseppe is in.**

 **Elena's POV**

I lay in bed listening to my own breathing dreading the day that was bound to come upon me. The sun was staining the glass, beaming through telling me to get up, but I could not. I knew _he_ would be arriving soon. Pulling the bed sheets over my head, I prayed I would disappear into the mattress becoming part of the bed.

Ever since Mother had told me about what Damon had done to his little sister, I had not known what to do. It troubled me as Damon was nearly the only person as free spirited as I was, and yet, he had been involved in his sister's death... or so I was told.

Damon had come the next day after we had met to join me for riding. I did not show. He had come every day since. I was wondering when he would finally give up.

"Elena?" There was a knock on my door. Emily opened it walking in gently. " _He's_ here.. and he claims this is the _last_ time he will come. Mother told him why you will not come out... he wants to exemplify things to you. What do I do?" She asked sitting on the edge of the bed. I closed my eyes and let out a deep breath.

"Tell him I do not want anything to do with him... it is only for the best. I am betrothed to his _brother_ , and that will be the extent of my relations to Damon," I felt as if a large weight was pushing me down further into the mattress. It was the feeling of giving up. There were no befitting men out there. I knew I wasn't giving him a chance, but I didn't know what else to do.

Doing nothing was all I _could_ do for now.

"Elena... it _could_ be gossip... what if he did not-"

"Emily, _please_! I _need_ time to think..." I interrupted her with a loud exhale.

"Very well.. I will leave you to your thoughts," Emily sighed. I knew she had gotten up because of the weight that lifted off the bed before hearing the bedroom door close.

Leaving me to my thoughts was nearly inconceivable when only a few minutes later the door opened rather loudly, and I knew it was Mother. Covers were ripped from my body. Cold air pinched every nerve on my skin. I shifted uncomfortably before sitting up and shivering giving Mother a cold stare.

"Elena! You have been in bed all day! It is nearly noon, and you are going to the Salvatore's today," she scolded before adding a smile as if she was giddy.

"What?" I asked.

"Yes! A letter came today from Giuseppe _himself_ wanting to meet you around three for tea," she smiled proudly. I sat up, and a cold sweat ran through my body.

" _Must_ I go, Mother?" I begged. "I have heard he is vile and cruel," I shivered remembering his bellowing voice I heard when I was a child.

"You _will_ do this for your family. This marriage alliance will bring the Salvatore's and Gilbert's closer together and wealthier than ever before. You _must_ go through with this marriage, Elena. Stefan Salvatore is a decent man, and he will bring this family fortune," she smiled.

"He believes I am an object he has won from his brother. He is not a decent man. He is not even a _man_. He is a boy," I stood from my bed. Trudy walked over handing me a dress for the day. I smiled and began to change behind the changing rack.

"And you are but a girl," she almost scowled. "Elena, you will _not_ start anything with me today, _do_ you understand?" She scolded.

"Will you accompany me to keep me in check?" I snipped from behind the rack.

"You will be going alone this time. Giuseppe has requested a singular audience from you, but you must be on your _best_ behavior do you _understand_?" She yelled not waiting for an answer before slamming the door behind her.

As I finished getting ready, Emily walked in once more.

"Emily.. I apologize for the way I acted earlier. I am just so _overwhelmed_ with Mother on my case and trying to let the Damon thing sink in-"

"Elena please... don't worry about it. I understand," she smiled sitting on the edge of my bed. I hesitated slightly before sitting down next to her.

"What did he say?" I asked curiously. Her mouth curved into a smile.

"Why did I know you would ask about him?" She asked herself. "He is upset. He wants you to know his whole story and not just some rumor made up by the townspeople. Damon fancies you, Elena... I can tell," she smiled.

"Don't be _absurd_ , Emily! We met _once_ ," I shook my head. There was no way he had feelings for me. That never happens. He doesn't even know me.

"I am just telling you what I saw. If he didn't care about you, do you think he would ride all the way on the other side of town for nine days straight?" She smirked. I thought about it as my mother called from downstairs.

"Elena you _better_ be ready! Aaron has prepared the carriage and is waiting!" She yelled from the bottom of the steps.

"I'm coming!" I called back. Letting out a heavy sigh, I turned to Emily. "Father has arranged a marriage with the younger Salvatore brother. It does not matter if Damon has feelings for me," I claimed as my voice almost cracked on his name. How could he have feelings for me? I was just a spoiled little rich girl. Was it my money? Was he desperate for a wife just like his brother? Was he trying to win me _from_ his brother?

"Elena!" Mother yelled again.

"If I do not go now, Mother will lecture me on the importance of time management," I rolled my eyes taking a stand.

"I wish you the best of luck," Emily smiled.

"Thank you Emily," I smiled walking near the door.

"Oh and Elena?" She stood. I turned around.

"Yeah?"

"When have you _ever_ let anyone control you? _Especially_ Father?" Emily asked with a small smirk. "If you have feelings for someone other than whom Father has arranged a marriage with, you know he will do anything to please you.. you're not trapped," she nodded. I walked out the door and down to Mother who was crossing her arms and tapping her foot looking like an extreme cliché.

"Elena, your tea with Giuseppe is in fifteen minutes, and it is a ten minute carriage ride there. What have I always told you?" She snipped.

"Being on time or later implies unimportance," I sighed before mumbling to myself, "which it is to me.."

"What did you just say?" Mother scolded.

"Nothing. I will tell Aaron to hurry," I nodded before walking out the door, giving Aaron a look of annoyance and stepping into the carriage.

The carriage ride over seemed far longer than it actually was. In about ten minutes, the carriage came to a halt.

"We are here Miss Gilbert," Aaron opened the door and held out his hand. I reached for it gently stepping down onto the gravel. We were in front of _Madame Charbone's,_ which was a tea and pastry restaurant and shop for the wealthy.

"I am not sure about this.." I said more to myself than Aaron.

"It is alright, Miss. You will do just fine, and if you need me please.. I will be right outside," his voice was extremely reassuring, so I nodded taking a step into the restaurant. A woman from the wait staff came up to me.

"Reservations?" She asked. Elena nodded. "Name?"

"Gilbert, Salvatore," I replied as her eyes bugged.

"M-Miss Gilbert. It-it is truly an honor meeting you. Mr Salvatore says he will be a minute or two. He is dealing with business at the moment. Would you like me to show you to your seat?" She asked. I shook my head.

"I think I will look around at samples for a bit. Have my camomile tea and sugar ready for me when I return," I nodded.

"Right away Miss," she claimed nearly jogging to fetch my tea. In the back of the restaurant, there was a small shop for specific kinds of teas. Emily loved tea, and her birthday was coming up rather quickly.

I had kept busy for almost twenty minutes before someone grabbed my arm. I jumped and turned.

"Damon?!" I nearly yelled.

"Keep your voice down, Elena!" He whispered pulling me closer to him. The hair on my neck stood up.

"Do _not_ touch me!" I hissed at the raven haired blue eyed man pulling away from him.

"Elena listen to me!" He almost yelled at me. I cowered away facing the opposite direction trying not to cry. "Give me ten minutes to explain.." I let out a deep breath calming myself and turned to face him.

"Get on with it then," I snipped. We were in a public space, so he would not harm me in any way if the rumors were true.

"About eight years ago, my sister, Giana passed away. She was only four years old. Stefan was nine and I was fourteen. She was the most _beautiful_ child I had ever seen. Giana looked like me in little girl form.. but cuter, and that's saying something," he chuckled. "She has curly black, long hair, ice blue eyes, and an attitude like no other. She was so full of life, so adventurous.." he looked down before back up again.

"July 17th, 1856. It was a clear day, and about a week before, my father had fired the stable boy and put me in his place. Do you remember me telling you about that?" He asked.

"Yes I do. You were in your father's study.. so he punished you," I nodded in remembrance.

"That is right. Because I was working the stables for punishment, that left Stefan as Giana's sitter. It was summer... so it was hot. Stefan wanted to go swimming. He had remembered my father teaching us boys how to swim at a young age. Giuseppe had thrown us in the nearby pond and waited for us to start treading on our own. Stef-Stefan _tried_ to do the same with Giana that day, not knowing any better. My father was strong, so when he threw us in, it was closer to the middle or deeper end of the pond. Since Stefan was _nine_ , he didn't throw Giana very far. She was fully submerged before Stefan had begun seeing the bl- the _blood_..."

Damon paused trying to gather himself to tell the rest of the story.

"That's when he began screaming. I was the _only_ one close. My father was in his study doing business with a client, and my mother and the maids were cooking lunch. I ran as _fast_ as I could to the scene. I dove in the water searching for my little sister until I found her _body_. She hit her head on a rock at the bottom of the pond, and _drowned_. I _tried_ to revive her.. I did... but it was too late. She was _gone_ ," his eyes were glistening, but no tears fell.

"Damon..." I whispered almost crying myself.

"I was _still_ doing CPR until my father and mother came to the scene from hearing Stefan wailing. My father knocked me over and began doing CPR himself until he realized she was dead. My father asked me what happened, and I was _too_ traumatized to even _speak_. I broke down, and he assumed I did that to her. He beat me until I passed out. My mother said he _almost_ killed me, and she had to pull him off of me. He broke my left arm, my collar bone and three ribs on my right side from kicking me so hard. Father's client witnessed the entire thing, and from then on out _I_ was the boy who drowned his sister on _purpose_. I _loved_ my sister. I wish she was here today. She would be twelve years old right now," he smiled to himself before shedding a single tear.

He wiped the tear away rather quickly and gathered himself, hiding his emotions.

"Stefan never told the truth, and even if I did, my father would never believe me and killed me. Stefan is his favorite child, so he could never do wrong.." he mumbled.

"I was sent off to military school the next week and came back around four years ago, yet the rumors still run rapid," he looked down. "Every year on July 17th, he beats me. Every year on April 3rd, he beats me. April 3rd is... was her birthday," Damon mumbled looking down.

"Is this the truth?" I asked. He nodded, and I knew he was telling the truth.

"Elena you _mustn't_ tell a soul. My father would literally kill me.." he trailed off with no overstimulation in his voice.

"Why are you telling me then?" I asked squinting my eyes.

"I am not really sure, Elena... I have kept it in _all_ these years, and I think I owe it to myself to tell someone. Plus, I figured you are good at keeping secrets," he curved his lips into one of the smallest smiles she had ever seen before making it disappear.

"But why me?" I asked still in shock Damon poured his heart out to me. "I mean surely you must have friends.."

Damon looked down.

"Oh my God you don't have _friends_?" Now I was utterly shocked.

"Well... I got the blame from my sister's death. _Not_ a lot of people were jumping out of their seats to be my friend," Damon shrugged before looking down. "You are pretty much it," he nodded not looking up to her eyes. "Other than my drinking friend, Alaric Saltzman, and my uncle," Damon smirked. "And the ladies of course," he winked adding to his smirk. I rolled my eyes ignoring the last comment.

"The town drunk?" I chuckled.

"Hey, he believed me, and he's an interesting man. He has a lot of stories. Alaric is a traveler," he shrugged.

"Or on the run from the police," I let out a laugh that made Damon smile.

"You have a great laugh, Elena," he nodded before raising his hand slowly brushing hair out of my eyes and tucking it behind my ear. The touch alone sent shivers down my spine. I looked up into his eyes and smiled warmly. He let go of my face and looked down. "Well... uh I should get going. See you tomorrow morning for riding?" I nodded. "Good luck with my father." His eyes grazed me up and down before exiting the store.

I let out a huff of air as my cheeks heated. Why was this man so intoxicating?

"Miss Gilbert?" I heard an older man ask. I jumped and looked to where the voice came from. "Hello, I am Giuseppe Salvatore. What are you doing?" He asked crinkling his brow.

"Oh.. uh the waiting staff said you would be a minute because you were in a business meeting.." I said with a nervous chuckle. "I was just looking at herbal mixtures as a gift for my sister's birthday coming up," I smiled.

"You mean that negro sister of yours? Yes, well, why don't we sit down and discuss your marriage to my son?" His face lifted in a polite smile, but his attitude remained cold and full of disgust.

"I would prefer if you didn't refer to my sister that way. Her skin color does not matter. We are all unique in different ways.." I nearly scowled.

"I did not come here to be lectured by a woman your age on matters such as slaves. Please have a seat," he gestured to the seat across from him. I sat as my blood boiled through my veins. "Tell me a bit about yourself, Elena," he raised the tea cup to his lips sipping lightly before setting it down.

"Well," I calmed myself. Stefan and Damon were not their father or so I hoped. I could tolerate this man. I could do it. "I am eighteen years old and was born right here in Mystic Falls. My father owns-"

"I know the basics, Elena. I want to know you. Tell me your hobbies.. your goals in life," he smiled.

"Very well. When I was a child I enjoyed exploring. I still wish I could beyond all of my daily chores around the house, however my time is limited. I enjoy animals.. mostly horses and cows. I find them fascinating. My brother Jeremy taught my sister and I how to read when I was young. I enjoy cooking, though I am not very good at it," I chuckled.

Giuseppe glared at me.

"My goals are to travel the world, be a genuine and kind person, to have a large family and make my life an adventure," I smiled.

"Your goals in life need to be adjusted my dear.." he chuckled darkly taking a drink. My smile disappeared.

"Excuse me?" I asked with a squint of my eyes. I hadn't been sure if I heard him correctly.

"You need to learn how your life goal needs to revolve around Stefan. Be the perfect wife. Learn how to make food, clean, have children. Make Stefan happy. Your wifely duties to my son are extremely important, Elena. He cannot have a rambunctious and uncontrollable wife when he has a business to uphold." I looked down feeling not much more than shame for myself. "He plans on meeting with you next Tuesday. You need to learn how to be a loyal and proper wife that will honor my son, or else I will find a different eligible bachelorette for Stefan," he waved for the check, paid and left me sitting there utterly alone and broken.

•••••

I cried the entire way home in the carriage and when my mother asked me about the tea with Mr Salvatore.

She hounded me on what went down of course. I slammed my bedroom door nearly in her face and hid under my covers. Not a few minutes later, the door opened softly. A dip was made in the bed from someone sitting, and the covers were pulled from my head.

"Father?" I asked curious.

"What is the matter my darling?" He asked raising a finger to dry his tears. He must have just come home from work due to the suit he was wearing and brief case by his feet.

"You cannot make me marry into the Salvatore family! They are racists! They hate Emily! I will not be married to someone who hates my family!" I yelled as tears rolled down my face.

"You must have met Giuseppe today, then," he shook his head in disgust. "That man is good at making business deals, and he is wealthy. However, I could never be friends with such a crass man," father tucked my hair behind my ear and poked my nose.

"Why would you marry me into that family, then?" I sobbed.

"Because, my darling.. he is a wealthy man. He is the only one in his family that treats people of color that way. The boys have different opinions. They were raised by a black woman when Lillian was extremely ill. She had been ill with some kind of disease for most of their childhood, so their maid, Nandi, helped raise the boys.." he explained.

My crying had ceased, and I was calm enough to listen what he had to say.

"I am not supposed to tell anyone this, so do not mention it to your mother. Giuseppe is very ill. He has not long to live, so he is trying to marry his sons off quickly," he nodded.

"Do Stefan and Damon know?" I asked.

"I am not sure, but it would be best if you did not mention this to them.." Father patted my hand.

"So, I assume _you_ switched the marriage agreement with Damon to Stefan because of what happened to their sister?" I asked.

"Yes. I will not put my daughter in any danger, no matter if the rumor is true or not," he sighed answering my question.

"In fact, Father, you have done quite the opposite.." I stood.

"What do you mean?"

"I know the truth about the death of Giana Salvatore. Stefan threw her in the river. Damon told me," I raised my chin. My father stood.

"Elena... please tell me you are not talking with that older Salvatore boy. He is nothing but trouble!" My father's voice was raising.

"Father, you know my ability to tell when people are lying. Damon Salvatore was not. Do you trust me, Father?" I asked grabbing his hand.

"Of course I trust you, my angel. It's just... I am only concerned for your safety. That is all," he nodded.

"I want to be clear. I do not think Stefan Salvatore is a cold hearted murderer. He was nine, and it was a mistake that will haunt him the rest of his life. However, because of his dishonesty and craving for affection from his father, he let Damon take the fall. He is Giuseppe's favorite child, and in all honesty... after what Giuseppe was telling me today, I believe he will do anything to make his father happy. I do not trust Stefan, but I do trust Damon.." I nodded.

My father crinkled his brow, pondering on what I had just told him.

"Do you have feelings for this Damon Salvatore?" He asked. I shook my head.

"I barely know him, but I do know I can trust him. He has not lied to me so far, yet Stefan has and has made non-gentleman-like actions towards me without my permission. Damon has treated me as a person, whereas Stefan has treated me like a business gateway for his father," I let out a sigh.

"What would you like me to do, Darling?" He asked.

"I would like to switch Salvatore brothers if I am to marry someone so quickly."

•••••

I was up early the next morning. Damon and I planned on going riding today, and I couldn't have my father find out. My father did not want me to marry a Salvatore. Even though he trusted me, he didn't trust Damon and especially not Stefan. I told him about Stefan kissing me after the meal, and he nearly flipped a table he was so angry. Father did not want to risk my own safety with the death of Giana Salvatore.

As much as my father wanted me married off, he did not want to hear about a boy kissing me or risk my safety. I was his little girl.

Was it so wrong to keep this from him? I mean it is not as if Damon and I are secretly together. He only wants to show me how to ride a horse and have fun... right?

Walking down the stairs at nearly dawn, I was in a dress, but grabbed Father's boots to wear for riding. Opening the door, Damon was sitting on the porch steps.

"I've been waiting, oh beautifully late one," he smiled taking a stand. Looking me up and down, Damon squinted. "Good luck trying to swing your leg over the horse. Good news for me, is that I get a little peep show," he chuckled. I hit his arm letting out a small laugh.

"This is all I have, Damon! Have you met my mother?"

"Yes.. sadly," he shook his head.

"What do you mean sadly?" I asked getting a little defensive.

"Your mother... I'm sure loves you and you love her, but she holds you back. She wants you to be everything a well-brought-up lady should be. The truth is... you need freedom. You want to be adventurous and spontaneous and unique. Not just another housewife," he smiled offering his arm to begin walking to the carriage. I took it before staring at him. "What?" He asked.

"How do you know so much about me? You barely know me.." I breathed.

"Because, Miss Gilbert," he opened the carriage door letting me in and climbed in after me. "You and I are the same. I was you growing up. I didn't want to be rich because I knew I didn't want the responsibility of taking over my father's company. I didn't want my entire life planned out for me, so I try to live life to the fullest," he smiled.

"Who's driving the carriage?" I asked realizing it was moving.

"My father's new stable boy, Jamison. He wants me to get used to the realities of being a wealthy man. We do not to grunt work, apparently. Father thinks we have blood made of gold most of the time," he paused with a sigh. "Plus, he has arranged a marriage he wants me to make time for. He had to scurry after John, your father, switched you to marry my brother. I know why too..." he looked down.

"I have to tell you something.." I looked to the ground.

"Yes?" He asked with a small intake of his breath.

"I honestly would like to marry you more than Stefan if I was to pick." His eyes whipped up to the side of my face. "I told my father of what Stefan did the day we had lunch, and how I am not comfortable marrying someone who treats me as an object instead of a person," I looked back up to him.

"What did John say?" He asked as his icy blue, intoxicating eyes melted into mine. He looked almost intrigued as if he greatly wanted to be married to me.

"My father said he would get me out of my engagement to Stefan, but would not let me marry you because he does not trust you.." I huffed.

"Because of what happened to Giana.." he looked down before jerking his head up. "This is exhausting. This Giana situation was completely blamed on me. I am done being pushed around because I am too scared and Stefan is too much of a goody-two-shoes to admit to what he did. My life is being planned out for me due to something that happened when I was fourteen. Life is not looking good for me. All my father could manage for a marriage was one of the girls he found working as a seamstress when my brother gets the gorgeous billionaire's daughter. I do not get to inherit my father's business. I always get the worst hand. I am done," he raged. "I am telling my father today," Damon nodded.

It nearly terrified me, but at the same time it sent a wave of exhilaration through my body.

"I do not only think of you as the billionai-"

"I know, Damon," I smiled.

"I am sorry I did not mean to snap in front of you," he apologized.

"Damon, you are okay. You make me feel dangerous.. not in a way that scares me, but a way that thrills me," I smirked. The carriage came to a slow halt.

"Oh really?" He smirked back. "You like danger?" Damon moved closer. His mouth coming closer to mine. I did not move. I could not move. I have never kissed anyone before. My heart began to pound extremely loud in my ears. I closed my eyes waiting, but nothing happened. Instead I heard the click of the door as his arm brushed my own.

I let out a breath opening my eyes. He was leaning in to open the door on my side.

"Just wait until you get on a horse. Full of danger, full of adventure and freedom. As the wind blows in your face, you will begin to feel as though you are flying..." he paused abruptly. "Are you alright?" He asked as my eyes turned to face his.

"Yes, just a head rush," I smiled with a small laugh. Although, I didn't have a head rush. For the first time ever, something consumed me. Something I had never seen coming or felt before.

It was Damon.

Damon Salvatore in his entirety had consumed my every nerve.

I wanted him to kiss me so bad, but what was I to do? It was not as though women could make the first move. That was the man's job, however, all I wanted to do was grab that incredibly chiseled jawline and shove my lips on his.

"Elena?" He asked grabbing my attention.

"Yes?" I asked.

"We're here," he nodded to a shop.

"I do not see your stable with horses, Mr Salvatore. All I see is a shop," I sighed.

"You are _not_ riding in that dress. My tailor will fit you properly for a riding outfit and boots that fit," he pointed to my feet where my father's large boots were.

"You mean I have to wear _pants_?!" I almost yelled in a whisper.

"Yes, Elena. Your mother will kill you if she finds your expensive dresses ruined from riding. Then you can have _no more_ adventures. We would not want that now would we?" He asked.

"I suppose you are right. I do not think I have ever worn pants in the _entirety_ of my _life_.." I mumbled actually wondering what it was like. It was extremely frowned upon for a woman to not be in a dress. I even wore a night dress to bed. This was going to be strange.

There's always a first for everything," Damon smiled opening the door. Hesitantly, I walked in. A hand brushed my bare upper back, and I shivered. "You know you can walk in right?" Damon smirked as he stood by my side.

"Damon!" The elder tailor walked up to him with a smile. "What brings you in today, good sir?" He asked with a smirk before looking at me. "Is _this_ the lady you were telling me about?" His smile grew. Damon's eyes got slightly bigger, and I swore I could see him blush.

"This is Elena Gilbert. She is betrothed to _Stefan_ ," he explained.

"Ooh... the girl that flipped brothers. Why didn't you stay with the elder brother? This guy's the _real_ deal," He asked with a slight chuckle.

"You mean Damon?" I laughed. "Women do not have voices in this world, Mr..?"

"Salvatore. Ooh you're _feisty_. I like you already," he smiled. I looked at him funny before looking to Damon. He stuck his hand out, and I shook it.

"Pleasure," I said politely.

"The pleasure is mine, Miss Gilbert," Mr Salvatore smiled bowing his head slightly.

"This is my uncle, Zachariah.. or Zach. He is really the only Salvatore that still cares for me other than my mother at times," he shrugged. "He knows the truth, and he's almost like my actual father," Damon smiled squeezing Zachariah's shoulder.

"Oh stop, you're making me blush," Zachariah shoved Damon playfully.

"Don't be a dick," Damon laughed shoving him back.

"Language, Mr Salvatore," I chuckled.

"My apologies, Miss Gilbert," he smirked at me making me shift uncomfortably where I was standing.

"Well.. shall we get you fitted for a riding outfit?" Zachariah asked with a smile to break the silence.

"Yes," I cleared my throat breaking away from Damon's enticing stare.

"I'm going to warn you, measurements for your pants may be uncomfortable. If you do not want to go through measurements, I can try to guess and go from there," he suggested.

"The second option may be better," I nodded with a gulp. I wanted this to be less stressful than it had to be.

"Very well, I will go in the back and grab a riding outfit," he smiled with a nod.

"You know getting measured is uncomfortable for _everyone_ ," Damon chuckled.

"Okay, but I am a lady. Having a man I met two minutes ago sliding his measuring string up the inside of my legs is not something I look forward to," I crossed my arms. He nearly looked me up and down while I was talking about my legs.

"You think men enjoy other men sliding their measuring string up our legs? We don't, but we do it to stay classy and elegant," His chin lifted slightly showing off his ego and not to mention sass.

"At least you don't have to wear corsets," I huffed.

"At least you don't have to take them off, men have to do that," he rolled his eyes.

"What are you talking about our servants do that?" I asked confused.

"Not all the time," he said with a wink and a sly smile.

My jaw dropped open.

"Mr. Salvatore, I do not wish to hear about your intimate times," I nearly choked out awkwardly.

"Oh don't be blushing now, Miss Gilbert. _Surely_ you've had a few of your own being as scandalous and free as you are," he chuckled.

"Just because I have a free soul, does not mean I spend it on the pleasures of men. I am perfectly fine and do have boundaries, Mr Salvatore," I snipped. "I would appreciate you not thinking of me in such a vulgar manner," I huffed as Zachariah came back out with a riding suit.

"You're a-" Damon began.

"Changing rooms are back there, Miss," he pointed to a small area where a curtain would cover everything but my ankles and lower calves.

"Thank you, Zachariah," I smiled taking the suit and sauntering over to the changing area. I got there and froze.

Well shit.

"Damon... would you mind undoing my corset?" I asked not looking him in the eyes. I would not ask Zachariah. I barely knew this man. Then again... I barely knew Damon.

"Of course," he claimed. I could almost feel his smirk. Getting away from prying eyes, he untied my dress in the back before kneeling and sliding it up my body. I shivered as he said, "up," in a husky, yet demanding tone. I lifted my arms, and he slid my dress off. I slid my corset cover off myself, as I knew how to do it myself. I could hear his breath stagger as my upper back was completely bare other than the slim straps of my chemise which was a long, thin dress under my corset that showed rather too much of my skin.

"No looking," I said rather quickly.

"No promises," he chuckled darkly from behind me.

"Damon!" I scolded.

"How do you expect me to take this off with my eyes closed?" He asked. I was silent. "That's what I thought," Damon's fingertips grazed my back briefly before finding the strings to untie my corset. The touch alone caused my belly to heat. What was this feeling? In nearly twenty seconds, my corset was completely untied. "Done," he said. I turned holding my corset to my chest. His eyes were still locked on my skin.

"That was quick."

"Lots of practice," he claimed smugly looking back up to my eyes. I could feel my cheeks heat in embarrassment.

"Behave yourself, Mr Salvatore," I warned with a raise of my eyebrows.

"Of course Miss Gilbert," he bowed his head briefly. As he was walking towards his uncle, he looked back as his eyes grazed my skin once more before looking away.

Entering the dressing room, I closed the curtain behind me. I undid the rest of my dress including my crinoline, chemise and drawers.

Pretty soon I was naked looking at the new outfit. Knowing how to put boy clothes on from helping teach my younger brother, I slid my pants on with ease before grabbing my corset once more.

"Damon?" I called.

"Yeah?" He replied.

"Could you help me put my corset back on?" I asked sheepishly peeking my head out. Damon walked over to me.

"I just took it off," he complained.

"I had to take everything under it off. I need you to put it back on," I claimed turning around and holding the front of it to my body. I would not have nothing but a shirt covering my breasts. I needed some sort of support especially since my chest wasn't small.

"Quite the scandal," I heard him muffled behind me. His hands were a bit shaken up as he touched my corset, and I knew I made him nervous.

"Excuse me?"

"Well, I usually have to pay to see this much skin on a woman," he suggested.

"Quit being so vulgar, Damon. You are merely helping a friend," I suggested as my face heated.

Once he began tightening my corset, I felt not as overwhelmed or exposed.

"Thank you," I smiled when he was finished.

"Finish getting dressed and we can go riding," Damon smiled walking back towards his uncle. I rolled my eyes.

After I had finished getting ready, I walked out feeling very strange and exposed. My pants were rather tight, however, Zachariah claimed it was supposed to be that way. My long-sleeve shirt hung over my pants for more coverage, and my riding boots nearly reached my knees.

"Why can I not wear a woman's habit again?" I asked shifting rather uncomfortably.

"Because, riding with both legs over one side is not living. It is following society's morals. Did I not tell you I would show you how to live properly with fun in your life?" He asked. I nodded. "It takes danger, adventure, and the thrill of being caught," he smirked grabbing my hand and whisking me into the carriage. "Did anyone ever tell you how fetching you look in men's clothing?" He asked nearly looking me up and down. The pants weren't skin thought, but a decently tight on my thighs. His eyes lingered there a bit.

"Where are we going riding today?" I asked sitting uncomfortably in the carriage.

"You'll see," was all he would tell me the entire way there.

After what seemed as an eternity, the carriage stopped.

"Where are we?" I asked looking out.

"Elena," he warned for the twentieth time.

"Right," I nodded. Opening the carriage door, I stepped outside, and my breath caught. "Beautiful," I breathed.

The carriage had stopped on a rather large hill, which seemed like a mountain. Below the hill was a beautiful open valley surrounded by the greenest of trees. I could see deer grazing in the open meadow from afar beside a lake. The sun shone on the water so beautifully, it looked as if the lake was a giant diamond.

"Where are we?" I asked one last time.

"I came here after what happened with Giana. I took one of my father's horses in the middle of the night, and I was planning on running away. I rode west, until I landed to this very spot. Behmer, the horse I had stolen," he pointed to the chestnut one with a black mane on the carriage, "hurt his leg. Once he began limping, I got down to help... but I was caught off guard. The moon was shining down on the lake, and I could see the entire valley. It was full of night animals. Deer were prancing around, eating. Owls and crickets were making sounds. All of a sudden, a rush of warmth came over me. I knew what happened. I could hear a soft angelic voice. The voice whispered something that changed my life forever. It said, "stay."" He paused looking over the valley. "It was Giana's voice."

I looked to the valley at the wild life with a small smile.

"I knew she wanted me to stay for something, but I haven't figured it out yet.." he looked down.

"Are you sure you heard a voice? It wasn't your mind playing tricks on you?" I asked folding my arms. He smiled quietly.

"I'm sure," he said before pausing. "Why don't we ride?" He asked with a sly smirk. I nodded, probably looking like a mad woman. Damon offered his arm taking me to the horses connected to the carriage.

"Which one am I riding," placing my palm on the black horse.

"Not him," he laughed to himself.

"What's wrong with this horse?" I asked dragging my fingers through his silky mane.

"Pharaoh is a two year old trouble maker. He is still in training to be a riding horse. Why don't you take his dam, Debutante," he nodded to the black horse next to Pharaoh. "She's nearly ten years old, and she is a well behaved broodmare," he smiled.

"Very well," I agreed as the new stable boy helped me prepare her for riding. "Thank you Jamison, for all of your help," I said with a smile.

"Of course, Miss Gilbert. Mr Salvatore, if either of you need anything please let me know," he nodded walking to sit at a tree's base with a small book.

"Need a boost?" Damon asked.

I didn't say a word, I merely put my foot in the stirrup, held on to the horn and boosted myself up swinging my leg over to the other side. Damon chuckled.

"Never mind," he nodded looking up to me before getting on Pharaoh. "Okay, to get the horse to walk, you click your tongue twice and tap their stomach once. Tap twice to trot and three times to run," he instructed with a demonstration of the first one.

I copied him telling Debutante to begin walking, and she began strolling next to Pharaoh. We walked for a while talking before he gave me a look.

"What?"

"Want to try trotting?" He asked. I nodded. "Lift your butt off the saddle slightly. It hurts like a bitch when they trot, and you are sitting down. Too much bouncing," he sighed. "Tap your heels twice and click your tongue, get off the seat and lean forward," he instructed before nodding indicating to do as he told.

I breathed in deeply. Yes I wanted to ride a horse like a man. I was all about adventure, but I was rather frightened.

"You're okay, Elena. If something happens I'm right here," he nodded. I looked straight forward again down to the pasture and followed his instructions. The horse did as she was told and began trotting. Damon was right. This was rather rough.

"Letting the horse run is so much more smooth than trotting," he sighed. My eyes rushed over to his. "Oh, no we will not be running today. Baby steps, Elena," he chuckled.

"Maybe I want to run," I shrugged. "Take a leap of faith, Damon. I am handling this better than other people would, don't you agree?" I asked. He nodded before looking me up and down.

"Im serious Elena, I am not sure how you look so dashing in men's clothing, but you do," he smiled.

"I know," I said with a wink.

Okay maybe I shouldn't be flirting, but I couldn't help it. Damon was a very attractive gentleman. I was being spontaneous today, so I had a right to flirt.

"Did you just wink at me Miss Gilbert?" He chuckled.

"Maybe," I smiled with a slight shrug of my shoulders.

"Don't be giving me the wrong idea, now. You know I'm attracted to you, so you doing that stuff is only going to make this worse for me," he shook his head raising the corner of his mouth.

"And why do you say that Damon?" I asked.

"Because I know I cannot marry you," he said bluntly before nudging his horse one more time and letting out a sharp "ya!" The horse took off in a dead sprint. Damon looked back expecting me to follow. I repeated his action, and my horse began to sprint. The feeling was incredibly free.

Then I thought for a second, what was stopping me from marrying him. Other than Jeremy, he was the only man who understood how I worked and without a question. Damon and I clicked well, and if we did marry, I knew it would be the most free I would ever be in my entire life. No other man would let me be free, run on the clear outside of the norms or even ride a horse as I was now. I mean I did not love Damon, but I knew it would be a good match.

I nudged Debutante, and I was off. My heart fluttered at the immediate increase in speed. It was not in fear, but in the thrill of the moment. This was one of my favorite feelings in the whole world.

The wind that hit me was immense and beautiful, like I would imagine flying would be like. As I caught up to Damon's horse, he looked surprised as if I wouldn't have Debutante run.

He proudly nodded to me, and then focused on the field. The horses ran, chasing the grazing deer around the pasture for about ten minutes. The horses slowed down and began walking to the lake for a drink.

"What do you mean you cannot marry me?" I asked avoiding all possible eye contact. It was a while before he responded. He was more than likely looking for the right words to say.

"We were engaged before you and my brother were. We are more alike than you are with him, and my brother is not ready for such a commitment quite yet. Have you not thought the same?" He asked.

"Oh I knew I wouldn't marry Stefan. He is too immature for me, and we are nothing alike. I will not be treated any less than a person. He treated me as if I was an object he won from you," I scoffed.

"He is a good kid. Stefan is too blinded by my father's overbearing need to be a dick and his business. He'll learn it's not all about business and success, but rather love and adventure that matters," Damon gave me a small smile.

"As for marriage I _am_ the one who tried to make the brother swap with my father. You and I are alike, and I know you will treat me as a person, not an object which is more than most men your age would do. You allow me to push my boundaries and help me in the process, and I really appreciate that," I smiled at him. "Plus you are handsome, charming and mysterious," Damon nodded looking down. Red flushed his cheeks, and he looked away.

"I didn't know you felt that way.." he nearly mumbled.

"I mean we haven't known each other for long.. I'm _only_ saying I would like a husband like that, which is why I told my father to make the switch," I chuckled nervously. " _Anyways_... who is this fiancé I've heard about?" I asked giving him a smirk.

"No need to bring that-" Damon was cut off by Jamison running and yelling towards us. There was another man waiting on a horse at the top of the hill.

"Elena!" He yelled. "Elena!" He yelled again before reaching us.

"What is wrong Jamison?" I asked worried.

"It's your sister, Emily.. she was killed."

 **Hey y'all I'm back. Life is hard man. College is hard, but I have not abandoned you guys. Sorry for that ending I love Emily and I was gonna build her character but I decided it would be different to kill her off. The real question is... who killed her? Leave a comment to who you think killed Emily. Otherwise I would love to hear your thoughts on this chapter and yes this is the longest chapter of any story ever I have probably written but oh well. Anyways, leave a comment, ask questions etc love y'all -Syd**

 **8130 Words**


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